Jonathan Rotenberg has worn many hats over his career—executive coach, management consultant, philanthropist, and now aspiring author. Although a graduate of Brown University, where he studied economics, and Harvard Business School, where he earned an MBA, Jonathan began to make his mark on the world when he was just a freshman in high school. In 1977, he started The Boston Computer Society, which soon became the leading international forum where computer companies unveiled their latest and greatest products to the public.
Jonathan’s success with BCS was covered everywhere from Time magazine to CBS Evening News, and the Association of Collegiate Entrepreneurs named him one of the “Top 100 Young Entrepreneurs in America.”
A dedicated meditator for decades, Jonathan has been a regular IMS yogi and donor since 2006.
This month, IMS’s John Spalding met with Jonathan at a coffee shop in Harvard Square, where they discussed Jonathan’s early success in business, his current projects (including the book he’s writing about Steve Jobs), and the path that led Jonathan to IMS.
Tell us about your spiritual path. How did you come to meditation?
Part of my spiritual path began with my experiencing an unusual level of success at a very young age. I cofounded The Boston Computer Society [BCS] in 1977, when I was 13 years old. I didn’t set out with a plan to succeed, or even with a clear idea of what I was doing. Still, the BCS took off crazy fast, becoming the most influential personal computer user organization in the world with 32,000 members in all 50 states and in 47 countries. When I was 19, I was profiled on the front page of The Wall Street Journal.
I earned fame and fortune but in reality was overcome with stress and worry. I was in a very powerful position where industry leaders would listen to me and follow my advice. Fame, fortune, and power—isn’t that what everyone craves who goes into business? It didn’t feel like a reward to me; it was an overwhelming burden. I felt personally responsible for so many people, and wanting everyone to have a wonderful experience.
With the peaks came valleys—identity crises and some serious spiritual questioning. Who am I? What’s my purpose? And it was through my early years at the BCS that I met Steve Jobs, who started me on my spiritual path. Steve introduced me to meditation and became a central teacher for me.
How did you meet Steve Jobs, and what can you share about the book you’re writing?
I met Steve in 1981, when I was 18 and he was 26. Steve was my hero. Apple had just gone public shortly before we met, and Steve went from being this, like, barefoot monastic without two nickels to rub together to suddenly being one of the greatest technology entrepreneurs ever—worth more than $250 million, which would be over a billion dollars today.
Steve had come to Boston for Applefest ’81, the world”s first international conference and exposition for Apple users. I was the creator and head of Applefest. I met Steve at the Top of the Hub for lunch, and we immediately hit it off. It was as if we’d known each other all our lives. We wound up spending 10 hours together that day. And at the end of the day, he walked me back to my parents’ house, where he gave me a gold pen with the Apple logo on it. Then he said, “On Monday morning, give my assistant a call. I’d like to fly you out to California, so we can talk more about all this.” That’s how our friendship began.
The book I’m writing is called My Teacher, Steve Jobs. Steve Jobs was an intensely devoted Zen Soto practitioner. He was an advanced protégé of Kobun Chino Otogawa and one of the most extensively read Buddhists I’ve ever met. My book tells the story of Steve’s own spiritual path—beginning in his early teens—and how he became the first leader in business history to integrate Eastern Wisdom teachings with Western Capitalism. It seems like a lot of people today have very strong (and often very negative) impressions of Steve Jobs. Once people understand more fully what Steve was trying to do—what he was trying to protect us from and what he was up against—I think people will begin to recognize the depth of compassion and wisdom that guided each of his decisions.
I look forward to reading your book. When did you start doing meditation retreats?
My first retreat was an LGBTQ+ retreat I attended in Santa Fe in 2000. It was an amazing experience, and from that retreat onward the LGBTQ+ community has supported me in my meditation practice and development. After I got back from Santa Fe, I started going to the Cambridge Insight Meditation Center, where I learned about Buddha Buddies, an LGBTQ+ meditation group that met at the Cambridge Zen Center. I started going to that group every Sunday. It was a wonderful sangha. It seemed like all of us were going through very difficult things in our own lives, but also together as a community, which was very supportive.
In 2009, several of us who had met through Buddha Buddies started a new “meta sangha” called OutBreath. OutBreath works with meditation centers of all different lineages to develop welcoming programming for LGBTQ+ people. We publicize our events on Meetup and have almost 3,500 members. We offer meditation classes, retreats, affinity groups, and workshops at centers around the Boston area.
I understand you’re involved with projects in Uganda that support their LGBTQ+ population.
That’s right. This year the Ugandan Parliament passed the 2023 Anti-Homosexuality Act (AHA), one of the most extreme, violent, anti-LGBTQ+ laws in human history. The law not only punishes LGBTQ+ people with life imprisonment and death but requires every Ugandan citizen to report to the police anyone they suspect may have “committed or intends to commit the offence of homosexuality.” Furthermore, it’s now illegal for landlords to rent to or house an LGBTQ+ person, which has led to a wave of evictions and homelessness. It’s absolutely mind-boggling.
I’m working with an organization called Create a Smile to Kids Uganda that provides emergency shelter, medical care, and crisis counseling for LGBTQ+ youth in Kampala who have been thrown out onto the street by their evangelical parents. I’m helping them with operational, security, and program issues, and raising money to fund their 2024 operating expenses. I created a GoFundMe page to help pay for food, shelter, security and other critical needs. People can visit if they’d like to learn more and help out.
Another organization I’m working with is the Uganda Minority Shelters Consortium, a coalition of 25 shelters across the country that secretly provide housing for homeless LGBTQ+ people. I’m now helping them to develop a U.S. fundraising strategy.
When did IMS enter your life?
I started going to IMS in the mid-2000s, right around when I left the management consulting business. At that point, I’d been a successful consultant for a number of years, working 70 to 90 hours per week. Basically, my life had been reduced to going from airports to car rentals to clients’ offices and back, over and over.
The tipping point was when I was working at AT&T’s corporate headquarters in New Jersey on a project that required pulling all-nighters. I slept on the office couch of the executive vice president who’d hired my firm. The afternoon we finished, I walked out of the building and had an extraordinary experience that’s difficult to convey. Suddenly everything around me became fuzzy. I stopped in my tracks, and l felt like I had literally died. I left my body, and I could see it below me, lying lifeless in the parking lot. I’d been feeling for some time like there was something spiritually missing from my life, but that’s when the realization hit me—I am dead. I wasn’t upset about it. “Oh,” I thought, “I have died. That’s interesting.” And in a way I really had died.
After that, I shifted the energy I had put into work into my spiritual practice. I did my first retreat at IMS in August 2006. It was a seven-day retreat with Howard Cohn, Mark Coleman, and Anna Douglas. That retreat changed everything for me, and I’ve basically done a retreat at IMS every year since then.
In what way was that IMS retreat a game changer?
[Laughing] I remember it now as being amazing and profound and unlike anything I’d ever done before. It felt life-changing to me, and it was! But I laugh because that’s not how I felt during the retreat. The truth is it was a real struggle for me, particularly the first couple of days. There were moments I wasn’t sure I could stick it out for the entire retreat.
Around day three, though, something shifted and I felt more settled. The wisdom of IMS teachers still always amazes me. They are so attuned to where you’re at that they’re able to suggest even slight adjustments that can help keep you going and move you deeper into practice.
Meditation classes and day workshops and retreats are wonderful, but nothing compares to what a long silent residential retreat can offer. I think of the retreats I did before IMS as like riding a bike with training wheels. When I got to IMS, the training wheels came off, and I discovered, Hey, I really can ride this bike!
But I see the importance of IMS as far more significant than that. It really is an international beacon for vipassana, for insight meditation. I think that as the world faces greater and greater challenges, interest in meditation will continue to grow, and IMS will have an opportunity to play a larger role.
A larger role in what sense?
There will be a greater need for highly trained and experienced meditation teachers. I think IMS has the potential to set the gold standard for meditation teacher training.
And as interest in meditation continues to grow, IMS will likely need to expand physically—to increase capacity. As it is, IMS retreats fill up fast and there are waiting lists, quite long waiting lists for some retreats. It hasn’t always been difficult to get into a retreat. Mind you, this isn’t a criticism of IMS. These are just growing pains, part of the price of success.